Ammonia → 1-(4-Amino-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 1006636ノート

反応式

HRID 1006636 の反応式
Cl[C:2]1[C:11]([NH:12][C:13](=O)[CH2:14]COC)=[C:10]([NH:19][CH2:20][C:21]([OH:24])([CH3:23])[CH3:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:25].[CH3:26][OH:27]>O.C(=O)(O)[O-].[Na+]>[NH2:25][C:2]1[C:11]2[N:12]=[C:13]([CH2:14][O:27][CH3:26])[N:19]([CH2:20][C:21]([CH3:22])([CH3:23])[OH:24])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

参加物

6

反応物 3

HCID 222AmmoniaHCID 887MethanolHCID 22672655N-[2-Chloro-4-(2-hydroxy-2-methylpropyl)amino-3-quinolinyl]-3-methoxypropanamide

生成物 1

HCID 100861791-(4-Amino-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
150 °C

実験手順

N-[2-Chloro-4-(2-hydroxy-2-methylpropyl)amino-3-quinolinyl]-3-methoxypropanamide (6 g, Example 110) was added to 5% ammonia in methanol (60 mL). The mixture was heated in a Parr bomb for 5 hours at approximately 150° C. The solvent was evaporated under vacuum to give a brown residue. The residue was diluted with water and sodium bicarbonate then extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over magnesium sulfate then evaporated to provide a tan solid. The solid was purified by silica gel chromatography to provide 1.64 g of the desired product as a solid, m.p. 174-175° C. Analysis: Calculated: %C, 65.0; %H, 7.0; %N, 17.8; Found: %C, 64.8; %H, 7.0; %N, 17.7.

後処理

  1. customThe solvent was evaporated under vacuum
  2. customto give a brown residue
  3. extractionthen extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthen evaporated
  8. customto provide a tan solid
  9. customThe solid was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-2120041e2e30474386919eb922a341d3
出典データセット
uspto-grants-2004_09
特許番号
US06790961B2

反応ノート

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